Sissy to Military School Pt. 03

The continuing story of Sissy Steffi at military school. If you haven't read the previous chapters, please do for context and back story. All characters in this story are of legal age. This story depicts the explicit erotica of a transgender nature. If this material is offensive to you; or forbidden in your area, or you are a minor, please stop reading! All characters depicted in this story are of legal age.

*****

Steffi & Kay have the talk and get intimate.

I awoke disoriented, not sure where I was. Had all that really happened? My ass was sore and bruised! My whole body ached. I could feel the crusty mixture of seamen and, whatever else, covering my backside. "Yes, it obviously did happen," I said aloud. Jack's arm was cradling me. His forearm running the length of my torso, his hand covering half my chest. Jack was asleep, big spooning me. I could feel his semi-hard cock nestled between my legs. "Oh no, I'm not waking that thing up!" I thought to myself. I was trying to stealthily slide out of bed without waking Jack.

"Hello, nice to meet you. What's your name sweetness?" Someone said from the other side of the room. I froze half crouching at the side of the bed. I was aware of my nakedness, a testimony of what happened presenting itself to this new audience of one.

"My name's Cedric," he said.

I looked up, my hands covering my pubic area in a futile attempt at modesty. I was flush red with embarrassment!

Cedric was seated across his bed. His back against the wall staring at me. Cedric was at least as tall as Jack, but not nearly as beefy. He was sinewy. He had deep, dark black skin. He was smiling as he was talking to me. His teeth were pearly white contrasting with his ebony skin tone. He was wearing a beige stocking hair cap. He wasn't wearing a shirt. His chest was defined, he had curly chest hair covering his pecs and deep cut six-pack abs. He was wearing a pair of Lakers yellow basketball shorts with purple trim, and hi-top tennis shoes. His hand was down his waistband casually fondling himself as he was talking to me!

Jack rose to a seated position on the bed. "Cedric this is my girlfriend Steffi," Jack said without looking back at Cedric. Jack stood rubbing his face in his hands; eclipsing my view of Cedric; or more importantly, Cedric's view of me! I started gathering my stuff off the floor.

"That's a fine fresh sissy bitch. You going to share?" Cedric asked Jack.

Jack was at his wall locker and threw a shirt at me. "Put this on Steffi."

It was a football jersey, with Jack's last name on the back. I put on Jack's Jersey. It fit me like a tent! The waist of the jersey came down to mid-thigh. I was wearing a football jersey dress! I craned my neck checking how it fit me from behind. My hips and ass were not as prominent. They did fill out the jersey, but only as curves.

Jack's voice boomed, "No I'm not going to share! She's not a bitch! Get out now!"

I snapped my head back to see that Cedric was no longer on his bed. The two were squared off face to face.

"I'm not going to be thrown out of my own room!" Cedric replied venomously to Jack.

Jack sternly nodded at Cedric. Cedric returned Jack's stern head nod, with a nod of his own.

I thought to myself, "What am I witnessing, some alpha male dominance ritual? Just like those birds on the discovery channel. What next, were they going to pound their chests at each other?"

Jack scowled his face turning red, a vein appeared on his forehead; and he said, "You will treat her with respect, and get out now!"

Cedric cocked his head to the side and replied, "Don't think I can't drop you. You big country fool!"

I saw Jack tense up. He was telegraphing that he was about to hit Cedric.

"I don't want to be in the middle of this if these two get into it. I'll probably be the one that gets hurt!" I thought to myself.

Raising my voice, I said, "Would you two stop it! You're both acting like brats on a recess playground! Try adulting for once!"

They both turned and looked at me with shocked expressions on their faces.

I scooped up my stuff and moved past them to the door stating, "I'm leaving now." As I passed through the door I looked back. They were still staring at me with wide-eyed surprised looks on their faces. I strutted down the hall to my room in Jack's football jersey.

Once I was in my room, it took me a minute sniffing the air. "Whew, I really stink! Oh god, my whole body aches. My entire ass feels bruised. My butt hole feels like a raw hamburger!" I mumbled. I stripped off my P.E. shorts and threw them into my wall locker.

I grabbed my shower kit and towel, back down the hall to the shower room I went. I still had Jack's jersey on.

I set my stuff on the bench and hung Jack's Jersey on the hook. I stepped into the shower and started washing my hair. It was greasy with oil and sweat. I lathered my washcloth and started with my crusty backside. There was crust from my anus all the way up my crack. I touched my anus with my soapy lathered finger.

What a mistake! "Damn that stings!" I said to myself. I couldn't rinse the soap off my crinkly rosebud fast enough! I cleaned the crust out of my matted pubes and washed from my thighs to my shins. I was now in my usual shower routine. Now that I was done cleaning the aftereffects of the sex from me. I finished my shower, grabbing my kit from the bench. I put on Jack's Jersey and went to the sinks to brush my teeth. This was the first time I had looked in a mirror since I left Jack's room. "Oh my god!" My neck was covered in hickeys! Not cute little love spots. Huge purple bruises covering both sides of my neck! I was marked! No one would have any doubt what I had been up to! I brushed my teeth, and then my hair in the mirror. I kept looking at those hickeys on my neck. There was no way to miss them, they were so prominent!

I gathered my things and walked back down the hall to my room. As I walked to my room it seemed as if everyone, I passed was looking at me. Looking at those hickeys! Someone even made a passing comment, "Damn baby, had a good time?" I flushed with embarrassment! Once I was in my room, I stripped off Jack's Jersey and threw it into my wall locker. Standing there naked, my asshole still throbbing, waves of confusion, self-doubt, and humiliation were consuming me. I remembered Kay's words from earlier.

"You have a lot of issues to work out. Come to my room. We can talk it out, girl to girl. I hope we can be girlfriends." If I had issues before, I certainly did now! I grabbed a pair of beach shorts and a half-cut belly tee-shirt, my cell phone; and back down the hall, I trudged to Kay's room.

I knocked on Kay's door. "Kay are you there?" I asked. "Kay if you're in there, please let me in. I could really use that talk." I said more urgently, knocking on the door a second time.

The door flew open, Kay standing there in a black silk kimono with gold dragon print. The kimono wasn't tied, completely open exposing Kay's nakedness except for a pair of red silk panties. How could Kay be so confident dressing in sexy women's clothes?

Kay put her hands on my shoulder's turning her head to either side inspecting me. Inspecting the hickeys on my neck.

"Well if it's not my sweet little sissy sister, not as naive as I thought!" She said. She walked back into the room dragging me by the shoulders.

Kay's room took me by surprise. The room was a two-person room, but there was only one bed. Instead of the drab green wool blanket on her bed, she had lavender satin sheets! In the middle of the room, there was a wicker chair with a plush velvet cushion on the seat. Instead of the harsh fluorescent lights, the room was softly lit by a standing bamboo lamp. There was a mini-fridge in the far corner of the room. At the end of the bed was a roll-top hope chest! On her desk were a Scentsy burner and a makeup mirror. I could smell the scent of pumpkin spice.

The wall locker was against the far wall. giving a nice open feel to the room. There was music softly playing from the TV in the corner, George Michael.

"This room is heaven!" I said as Kay closed the door behind us. "How did you manage it?" I asked?

"I do favors for the dorm supervisor," Kay replied, as he sat me in the wicker chair. I gingerly took my seat. The velvet cushion spared my bottom the pain I anticipated.

"Now you didn't come down to my room to discuss the room decor," Kay said, as he sat on the bed facing me, lighting a blunt.

"Tell me everything. Starting with who has you afraid to sit down and marked you with those nasty hickeys!" Kay said, inhaling from the blunt and passing it to me.

I blushed turning from Kay's gaze.

"Oh, aren't you the sweetest thing! I've been there too baby! All of us girls go through it. Welcome to the sisterhood!" His hands-on his knees waiting intently for my story. I took a long puff from the blunt.

"Jack did it." I blurted out.

I then opened up, pouring out a stream of consciousness to Kay.

I told Kay I was so confused. I vented about my stepfather, how he was so mean to me. He had shipped me away to here, a military school of all places!

"This place was so different from where I come from back on the beach. I hadn't ever thought of my sexuality. I know that I have feminine features, especially my ass. None of my friends on the beach noticed my ass or thought of me sexually! All the people on the beach were so nice to me; unlike the people here that seemed to just pick on me!"

I told Kay about the beach vendors, how they let me take shifts at their carts for tips. The nice guy Alejandro, at the burger hut that comped my meals. The guy at the surf shop; would pay me an entire day's pay for watching the shop for a few hours, while he went surfing.

"Everyone was so nice to me back at the beach! Here? It was terrible! Everyone teases me. Except for Jack. He was different. He bought me meals; and was so nice, he even paid my cell phone bill!" We pasted the blunt between us.

My cell phone chimed a text message alert. I was about to retrieve my phone from where I left it on Kay's desk.

Kay put his hands on my knees and said, "It can wait, honey, we're talking now."

Kay sighed and said, "Oh what I would pay to have that ass of yours! My sweet adorable, naive, naturally sexy sissy sister! You've been walking around your entire life dressed like that? Booty shorts and half shirts?"

"They're the only clothes I have. I usually get my clothes from the surf shop. I had to get my shorts from the girl's section because the men's shorts don't fit me." I replied, Inhaling deeply, and passing back to Kay.

"Let me guess, you didn't pay for your clothes at the Surf Shop?" Kay inquired.

"No Ron comped them for me," I replied.

"And Ron helped you pick them out I'll bet?" Kay said flatly.

"And you've never worn underwear at all?", Kay asked.

"Underwear, salt, and sand don't mix," I replied.

Kay let out a long sigh. "I see I'm going to have to give you the talk your mama should have given you a long time ago!" Kay stated.

"Your stepfather doesn't hate you. I think it's quite the opposite. He had to get you out of that house before he gave into irresistible temptation." Kay said.

The text message alert went off on my phone again.

Kay firmly gripped my knees. "Don't even think about it," Kay said sternly.

"Why do you think people were so nice to you at the beach?" Kay asked.

I opened my mouth to reply, Kay put his finger to my lips.

"If you're pretty, people do nice things for you. Life is easy." Kay stated.

"Not nice, old Alejandro from the burger hut!" I interrupted.

Kay cocked his head and in a teasing high-pitched voice said, "Especially nice old Alejandro. Men only feed you if they want to fuck you." and we both giggled.

Kay then stated, "Ron at the surf shop? I'll bet not only did he help you pick those clothes out; I'll bet he helped you try them on. He was getting a striptease for the cost of an outfit! Maybe even some touching? He was grooming you, baby!"

The text alert went off on my phone again.

"I really have to get that," I said, as I stood to retrieve my phone.

Kay stood with me. His face inches from mine. He took both my hands in his. He moved in and kissed me gently on the lips and whispered, "Don't you dare. This is my time!"

Kay then said, "Now about this Jack, here at school. He landed the hottest piece of ass I've ever seen! This is an all-male, military school. Sissy's and gays are a hot commodity around here. All the alphas try to snatch us up early. All the other guys are teasing you because they want you too! They just don't know what they're doing. Almost everyone here is from real money. They're castoff kids. For whatever reason, their parents didn't want them around the house."

"Like me," I replied.

"No not like you, you've been teasing these boys and didn't even know it. When you accept yourself for who you are, you're going to have real power baby."

My text message alert on the phone went off again.

"Whoever that is, they're persistent," Kay said as he spun me around.

"Bend over, put your elbows on the seat of the chair," Kay said as he had his hand on my shoulders pushing me over and down.

"Not you too. I thought we were sisters!" I protested.

"Don't worry honey, I'm just being your concerned sister. We need to see what kind of damage Jack did back there. You were a virgin after all!"

"I was a virgin," I repeated. I complied by bending over at the waist, my elbows in the seat of the chair.

Kay grabbed the waistband of my shorts and pulled them down to my ankles. His face was right next to my ass. I could feel his hot breath on my cheeks. I stepped out of my shorts. Kay told me to spread my feet apart. I spread my feet as he instructed, and he spread my cheeks. I felt Kays breath on my puckered rosebud. With my cheeks spread, I could feel the sharp needle pain in my anus.

"You have a love bite on your cheek. Oh my, he did wear that boy pussy out! There's some bruising and inflammation, but no permanent damage. I have just the thing for this. You stay right there." Kay said and moved to the hope chest at the end of the bed. I heard Kay rummaging through the hope chest, but from my position, face down in the seat pillow, my legs spread, and my ass in the air, I couldn't see what he was doing.

"Here it is!" Kay said, taking a position behind me. "Oh my god, you have such a perfect ass. I would pay real money to have that ass!" Kay said as he crouched behind me. Gripping the top of my ass with one hand. I gasped as I felt something cool and wet on my anus. It was immediately soothing! The hot needle pain in my anus was gone, replaced by a cold wet sensation.

I heard and felt a pop, I felt something bulbous penetrate me. It filled a spot just behind my anal ring. Nothing like what Jack had done. It just seemed to fit. The soothing cold wet sensation on both sides of my anal ring.

I sighed with relief!

"OK stand up now honey," Kay said.

I could feel it inside me, as I stood. The cool sensation dominating my crinkled hole.

I stood and turned to thank her.

"Thank you, what was that? It's such a relief!" I told Kay.

"It's a stainless-steel trainer butt plug, covered in mentholated anal gel," Kay said.

Lube the plug every night and insert it before you go to sleep, don't wear it at P.E. Running can make it pop out. You can wear it walking around. Clean it every day." Kay instructed.

Kay was holding the tube of gel in one hand, and a piece of fabric in the other. "It won't do for you to be going commando around here. I feel honored to give my new sister her first pair of panties!" Kay said as I took the panties and tube of gel.

"They're too small for me," I said, inspecting the tiny bit of fabric in my hand.

My cell chimed again, another text message.

I didn't even look over at the phone this time. Still inspecting the gray triangle with blue trim and an elastic waistband.

Kay explained, "They're nylon sports thong panties. They stretch, try them on." I stepped into the panties and pulled the elastic waistband into place on my hips. I craned my neck to inspect how it fit my backside. The triangle material wedged and melded into the top of my ass cleavage. My cheeks were completely bare. I ran my palm over my pubic mound that was covered in the nylon fabric. I was delighted how the nylon stretched and compressed my tiny knob against my pubic mound!

Just then Kay broke my attention and said, "Oh honey that just won't do. You've got a Texas tumbleweed down there!". Kay was right. I had focused on the triangle of fabric suppressing and concealing my tiny cock, but there were long patches of blonde pubic hair escaping from every angle at the edges of the panty bottoms. Kay was rummaging through his hope chest again. My eyes widened with anxiety as Kay stood from the hope chest, a pair of cordless electric hair trimmers in his hand.

"Oh, honey don't worry I know what I'm doing. These are professional trimmers. I've done this a hundred times." Kay said, and then with a flourish pulled his own panties aside.

"See not one hair to be found. doesn't it look pretty when it's clean?" Kay exclaimed. I took in the whole picture. Kay was so dark and exotic. He had straight black hair. I gazed at Kay's chest, it was bare and smooth. His nipples were lighter colored, about the size of a nickel, and his nipple tips were erect like two pencil erasers. His abs were slightly defined, but not dominate. His treasure trail had not been shaved. It pulled your focus lower to his groin. I've already described Kay's cock. It was seriously almost as thick as my wrist! The cockhead as large as a golf ball, it was a well-defined bell, flaring at the edges. His shaft was nearly as thick as my wrist! A thick vein running from his balls to the bottom of the bell. His balls were as impressive as his cock! His scrotum tight, encasing balls that must be storing a quart of spunk! All was smooth, slick and bare. I remembered my relief that Jack's cock wasn't a monster like Kay's! I know if it had been Kay instead of Jack, my poor ass would have been split from my taint to my tailbone! I startled as Kay stepped toward me.

"Oh baby, does Kay's she-monster frightened you? Don't worry baby this isn't for you." Kay said with a playful mocking tone and a light chuckle. He tucked his cock back into his panties.

Kay moved me over to the bed and I sat on the edge. Kay looked and me and said, "OK sister, shaving your pussy doesn't work unless you take your panties off." Kneeling to eye level with my crotch and; click buzz, starting the trimmer as if to punctuate his sentence. I lifted my ass off the bed and peeled my panties down slowly. Kay licked his lips as my pubic mound with all my blond pubes was revealed. Kay helped me pull my panties past my knees and down to my ankles with his free hand. I lifted my ankles to help Kay remove my panties completely from my feet. Kay threw the panties onto the bed beside me. Kay grasped both of my ankles with his free hand pushing them up, forcing me to a reclined position on the bed. My head was swimming from the effects of the pot. It was incredibly potent!

Kay's face was so close to my groin I could feel his hot breath on my cock head and balls. I felt the buzzing vibration as Kay ran the trimmers over my pubic mound. Kay grabbed my penis with his fingers moving it to the side to trim the pubes. The trimmer's buzzing and vibration were getting me aroused.

"Feels good doesn't it sissy?" Kay said as he lifted one of my balls with his fingers. I moaned as Kay ran the trimmer under the ball he had lifted with his fingers.

Kay ran the trimmer back up my pubic mound and squeezed both my balls between his fingers. The vibration seemed like it was stimulating my nerve endings all the way to my nipples! The feeling was intense! I squealed with delight as I grabbed my nipple pulling and twisting it. Kay lifted both my balls and placed the back of the trimmer blade against them as he shaved down my taint. The vibration sent shockwaves throughout my pubic area, taint and even my thighs!